112111-44-1

Basic information

• Product Name: Acetic acid, [(S)-(diphenylMethyl)sulfinyl]-
• Synonyms: Acetic acid, [(S)-(diphenylMethyl)sulfinyl]-;(S)-(+)-Modafinic acid;[(S)-(Diphenylmethyl)sulfinyl]acetic acid;(S)-((addition))-Modafinic acid
• CAS NO: 112111-44-1
• Molecular Formula: C₁₅H₁₄O₃S
• Molecular Weight: 274.33486
• Mol File: 112111-44-1.mol
• Article Data: 7

Chemical Properties

• Melting Point: 185-188℃
• Boiling Point: 539.2±50.0 °C(Predicted)
• Appearance: /
• Density: 1.327±0.06 g/cm3(Predicted)
• Storage Temp.: -20°C Freezer
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: 2.83±0.10(Predicted)
• CAS DataBase Reference: Acetic acid, [(S)-(diphenylMethyl)sulfinyl]-(CAS DataBase Reference)
• NIST Chemistry Reference: Acetic acid, [(S)-(diphenylMethyl)sulfinyl]-(112111-44-1)
• EPA Substance Registry System: Acetic acid, [(S)-(diphenylMethyl)sulfinyl]-(112111-44-1)

Safety Data

• Hazardous Substances Data: 112111-44-1(Hazardous Substances Data)

Usage

Description

Acetic acid, [(S)-(diphenylmethyl)sulfinyl]-, also known as (S)-(+)-Modafinic Acid, is an organic compound that serves as an intermediate in the synthesis of Modafinil and related compounds. These compounds are known for their neuroprotective properties, which can be beneficial in various medical applications.

Uses

Used in Pharmaceutical Industry:
Acetic acid, [(S)-(diphenylmethyl)sulfinyl]is used as an intermediate in the synthesis of Modafinil and related compounds for their neuroprotective properties. These compounds are known to have potential applications in the treatment of various neurological disorders and conditions, such as narcolepsy, sleep apnea, and shift work sleep disorder.
Additionally, due to their neuroprotective properties, these compounds may also be explored for their potential in treating other neurological conditions, such as Alzheimer's disease, Parkinson's disease, and multiple sclerosis. The development of new drug delivery systems and formulations can further enhance the efficacy and bioavailability of these compounds, leading to improved therapeutic outcomes in various medical applications.

Upstream product

• 63547-24-0 modafinil acid 
• 827603-88-3 2-((S)-Diphenyl-methanesulfinyl)-1-((R)-4-phenyl-2-thioxo-thiazolidin-3-yl)-ethanone 
• 63547-22-8 (benzhydrylthio)acetic acid 
• 91-01-0 1,1-Diphenylmethanol 
• 63547-23-9 (diphenylmethyl)(ethyl acetate)sulfide 
• 118286-19-4 (diphenylmethyl)(ethyl acetate)sulfoxide 
• 112111-45-2 (R)-Modafinil acid 

Downstream Products

• 865811-65-0 (S)-(+)-methyl (diphenylmethanesulfinyl)-acetate 
• 112111-45-2 (R)-Modafinil acid 
• 63547-22-8 (benzhydrylthio)acetic acid 

Relevant articles and documents

Asymmetric Oxidation Synthesis of Modafinil Acid by Use of a Recyclable Chiral-at-Metal Complex

The enantioselective oxidation synthesis of chiral modafinil acid and its analogues with high enantiomeric excess has been developed by means of a chiral-at-metal strategy. Treatment of ruthenium complexes cis-[Ru(bpy)2Cl2] or Δ/Λ-[Ru(bpy)2(MeCN)2](PF6)2 (bpy is 2,2′-bipyridine) with the appropriate prochiral thioether ligands afforded thioether complexes rac-1, Δ/Λ-1, rac-2, Δ/Λ-2, rac-3, and Δ/Λ-3. Diastereoselective oxidation of the thioether complexes in situ produced the corresponding sulfoxide complexes rac-1a, Δ/Λ-1a, rac-2a, Δ/Λ-2a, rac-3a, and Δ/Λ-3a. The configuration at the metal center in each case is stable during the coordination and oxidation reactions, and dictates the chirality of the sulfoxide ligand in the oxidation process. The chiral modafinil acids were obtained with ee values greater than 98% upon their removal from the corresponding sulfoxide complexes in the presence of TFA/MeCN. Moreover, the chiral ruthenium precursors Δ/Λ-[Ru(bpy)2(MeCN)2](PF6)2 are recyclable and reusable with complete retention of the configurations. Chiral modafinil acid and its analogues have been synthesized with high ee values by means of asymmetric coordination oxidation of a thioether complex in situ with a chiral-at-metal strategy.

A PROCESS OF SULFOXIDATION OF BIOLOGICALLY ACTIVE COMPOUNDS

The present invention relates to a new process for the preparation of sulfoxides, preferably stereoselective preparation of substituted or unsubstituted chiral sulfinyl derivatives 2-(2- pyridylmethyl) sulfinyl-l H-benzimidazole by oxidation with oxaziridine in presence of suitable solvent and base.

Microbial oxidation/amidation of benzhydrylsulfanyl acetic acid. Synthesis of (+)-modafinil

A highly enantioselective oxidation of benzhydrylsulfanyl acetic acid to the corresponding (S)-sulfinyl carboxylic acid was achieved employing the fungus Beauveria bassiana in very good yield. This product was amidated using the bacteria Bacillus subtilis to afford (S)-modafinil in good yield.